2, 4-dihydroxydiphenylethane and process of making it



Patented Aug. 17, 1926.

UNITED STATES EMIL KLARMANN, OF JERSEY CITY, NEW JERSEY, ASSIGNOB TO LEHN & RINK, INC.,

01 NEW YORK, N. Y., A CORPORATION OF NEW YORK 2, 4-DIHIYDROXYDIPHENYLETHANE AND PROCESS OF MAKING IT.

Ho Drawing.

This invention consists of the novel organic product specified and the method of making it, which product possesses valuable therapeutic properties, and, more especially, as an internal antiseptic.- It has a high germicidal action, and especially as regards B. typhosus. Its phenol coeflicient as determined by the standard method of the U. S. Hygienic Laboratory is approximately 43, whereas its toxicity is remarkably low.

In a previous patent application, Serial No. 61,335, filed October 8th, 1925, have specified that 2, 4-dihydroxydiphenylethane shows a high phenol coefficient and at the same time a low toxicity which would justify its use as an internal antiseptic. I have now found that 2,4-dihydroxydiphenylethane shows a similar behavior The way to obtain it is different from that in the case v ide.

of the dihydroxydiphenylmethane. A ketoimidohydrochloride is first obtained by the condensation of resorcinol and benzyl cyan- This is then transformed into the metadihydroxydeshydroxybenzoin (2,4-dihydroxyphenylbenzylketone), the latter being reduced to the 2,4 dihydroxydiphenylethane.

The process may be graphically illustrated by the following equations:

Owners Oar:

' grams of resorcinol and 5 grams of benzyl cyanide are dissolved in 40 cc. of dry ether and 2 grams of dry ZnCl are added. A current of dry HCl is allowed to pass through this mixture for 2 to 3 hours. The flask is allowed to stand in an ice box over night. Then .dilute HO1 (1:1) is added. A, yellow crystalline precipitate of the ketoimldohydrochloride soon forms. accelerated by vigorous shakin of the flask or rubbing with a glass rod. The precipitate The formation is 1 Application filed December 15, 1925. Serial No. 75,619.

is freed from the unchanged raw materials by ether, dried and dissolved in 500 cc. of

water. It is then boiled under reflux for 25 minutes. The keto compound precipitates in the form. of needles upon standing. It may be recrystallized from water. m. p. 121 C. -(uncorr.) dark red coloration with dilute F e01 The compound thus obtained is now reduced by heating with HCl (1:3) and amalgamated zinc for 16 hours. It crystallizes from water in flattened needles in. p. 131 C. (uncorr.)

Analysis 10.573 mg. give30,090 mg. CO and 6.780 mg. H O i, e., 78.06% C. and 7.21% H.

Theory C I-I 0 77.75% C. and 7.46% H.

structurally the graphic formula of the new product is OH r 2. The process of making 2,4-dihydroxydiphenylethane, which consists in first forming the corresponding ktoimidohydrochloride, then transforming this product into metadihydroxydeshydt'oxybenzoin (2, 4 di hydroxyphenylbenzylketone),. and finally reducing the productfto 2,4' di'hydroxydiphenylethane. v

3. The process which consists in making 2, 4 dihydroxydiphenylethane by the reduction of meta dihydroxydesoxybenzoin (2, 4 dihydroxyphenylbenzylketone) In testimo' y whereof I have signed the foregoing specification.

EMIL KLARMANN. 

